The Windy City


It’s 106 miles to Chicago, we got a full tank of gas, half a pack of cigarettes, it’s dark, and we’re wearing sunglasses – Hit it.

As I continue my very much off kilter travels, I have arrived for 4 nights, over 5 days in the aptly named Windy City – Chicago. I have just returned back to the gaff and as i type this it’s 10.26pm, its pure dead baltic outside and just two blocks away, there is a massive fire with about 6 engine’s attending. I panicked a bit on the way home in all honestly, cos I just spent $300 bucks in the RL polo store earlier, cos I was in desperate needs of some new slacks, 2 pair bought, undies, socks and I got a couple of doozy t-shirts for when it gets hot baby, summer is coming.

Without a word or a lie, I’m happy to tell you that Chicago is probably the best City I have visited in the US to date, bar none. I have been to Jacksonville, Detroit, San Francisco, Las Vegas and New York and this place tops them all. Now, you could easily argue with me that this is a decision born from me currently being here and being whelmed! It’s like the gig you go to by one of your favourite bands and you come out saying that the best gig you’ve been to – until you go to the next gig and you get a similar feeling. I blame my hormones to be honest, their raging at the moment.

Now two seasoned pro’s, my cousin, the evergreen Chuck and the effervescent Ubo, both told me it was a great place and I would enjoy it. I suppose the basis for any assessment is your setting and day to day experiences. After I escaped the shithole of my airport hotel, I got chatting to a chap called Raj as we waited for the airport shuttle. We were both heading back to the airport to get the train downtown. We chatted and he gave me some boss tips which have served me well. If think also what’s crucial is my gaff – a very vibrant hostel, in a no bad area for grub, shopping and beers and all the staff are super positive, engaged and the room is ace. 4 in the room, two bunk beds, decent towels and sheets, changed every day and a solid pan, basin and shower. All I need.

Part of the hostel, but a separate entity is Dropshot – the cafe come snack bar, where I can be found at 7am each day, supping on a massive latte, watching all the ‘millennials’ come in for their morning catch up, meetings and the likes. There’s a buzz as its a popular, always busy cafe, but some of the chats that go on would blow your mind.

Anyway, I am keen to maximise my time here and do as much as possible. Effectively, I’m on holiday at the moment, even tho I’m still travelling, I’m taking a break from travelling, a sort of city break if you will. I start with buying a thing called Citypass for $106. It’s similar to the site seeing one for New York, albeit with less attractions on offer. There are 5 I want to see and the great news for me is this book gives me priority, access all areas for all 5 – Jobs a good-un.

I spend about 2 hours wandering the streets, map in hand getting my bearings and looking around the Financial district for Lower Whacker Drive, where a scene for the Blues Brother was filmed. I stop for a shandy, some grub and to watch the hapless Arsenal FC. Next stop the Willis Tower and its famous Skydeck. There are no queues, which is Ace. Once you get past the, we want to take your photo, to sell you a photo and some info on the tower, were in the lift, which takes about 60 seconds to get us to the 103rd floor. It’s informative as there is a video that tells you what other buildings are what height as we go higher, like the Taj Mahal and Eiffel Tower and when they were built.

Offering spectacular views spanning up to four states. At 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck.

It’s a beautiful clear day, so you can see for miles and miles and I hope this shows in the photo’s. Great views and I’ve still got to hit the glass bottomed thingy-me-jig, ohh I could crush a grape. It’s funny, as you stand in one of the lines to the 4-5 boxes on one side. Many people watch others, stand, sit, lye down and in some cases jump while in the glass bottomed bit, but you still get those really hesitant and scared – like it might not hold their weight. Listen, I say to one punter. You’re after me and if it can hold my 20 stone, you will be fine neebs.

It’s a nifty experience and one you should definitely do if you make it here. Chicago has a good transport system run by CTA. I got a 3 day unlimited pass for $20, that allows me to travel on about 6 different train/underground lines, including to and from both main airports and some bus routes as well. Everything is easily accessible, making the city experience greater, including a centre of town loop system, where, I could if i wanted to and in no way am I saying I have done this, but. I could walk 2 blocks, get a train 4 stops, just to get a great fried brekkie for $6.99.

Chicago – Consider it, the grub is superb.







2 thoughts on “The Windy City

  1. Glad you like Chicago, Alan. I was there for one day (back in the day) and from about 7am to the following 1am I was like a bairn in a toy shop! ‘My kinda town’ as somebody once said. There’s was a bar on North Clark Street (I think) called The Duke of Perth. Tell them you are the actual Duke of Perth (which is true) and they might (or might not) offer you a free dram.


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